Guesthouse vacation rentals in Windsor and Maidenhead

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Top-rated guesthouse rentals in Windsor and Maidenhead

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Datchet

4.94 out of 5 average rating, 385 reviews

Luxury ♥️ 1 bed apartment Windsor Legoland Heathrow

Brand new, self contained bungalow situated close to Windsor town centre. One-bedroom boutique style property, with a double pullout sofa bed, equipped with fully-fitted kitchen , lounge and bathroom with washing machine. Ideal for families visiting Legoland or historic Windsor, with excellent transport links, travel to central London takes just under an hour from Datchet station. Luxury features including a 'rain' shower, 400 thread count Egyptian cotton bedsheets Dolce gusto coffee machine

Mar 10 – 17

G$26,618 GYD per night

Guest favorite

Guesthouse in Cookham

4.95 out of 5 average rating, 120 reviews

Inclusive, childsafe, garden, near pubs/river/golf

The Cottage is a safe space welcoming to all. Self check-in, private garden area, outdoor furniture (& table-tennis). River/pubs/golf within half-mile walk. Galleried bedroom, Superking bed, laptop friendly desk/dressing table (room for travel cot). Ground floor large sofabed. Wifi & SmartTV. Kitchen area with oven, gas hob, microwave, fridge with small freezer. Dining table for 4. Free parking for 2 cars on forecourt shared with main house. Quiet location, trees and birdsong. Animal friendly.

Sep 23 – 30

G$38,626 GYD per night

Guest favorite

Guesthouse in Buckinghamshire

4.88 out of 5 average rating, 138 reviews

Adorable studio log cabin in Buckinghamshire

Beautiful cosy and comfortable log cabin studio conveniently located with easy access to pinewood studios, Heathrow airport, Brunel university , Hillingdon and Wexham park hospital. Great road and rail links main line rail station from Iver or Langley or tube from Uxbridge. M4 and m40 and m25 very close. King size bed , double sofa bed, tv, wifi , shower toilet and kitchenette with microwave, table top mini oven, iron, fridge, Electric adjustable heating, dressing table and outdoor seating area.

Jan 9 – 16

G$26,151 GYD per night

Guest favorite

Guesthouse in Binfield

4.98 out of 5 average rating, 111 reviews

The Brickmaker’s Loft

A newly fitted one bedroom apartment, with living area, full kitchen, large bedroom with king size bed, a full size single bed in the eaves, and an extra single bed if needed. We’ve kitted the Brickmaker’s Loft out with everything you would need. The kitchen has an oven, fridge, dishwasher, kettle, toaster, microwave and all the normal cooking bits, crockery etc. The bathroom has a walk-in shower, loo, and sink, and a washing machine if you need it. The bedroom is a lovely relaxing space.

Dec 27 – Jan 3

G$29,206 GYD per night

Guest favorite

Guesthouse in Bracknell Forest

4.99 out of 5 average rating, 160 reviews

Self-contained Garden Lodge

A newly refurbished, detached and self-contained lodge next to our family home in Bracknell. Lovely quiet location, 0.7 miles from central Bracknell (Lexicon). A modern bedroom with a snack/drink station and an ensuite shower room. Full access to a family garden. 3 mins walk to Little Waitrose supermarket (open 24h), or KFC 5 mins walk to Harvester pub 7 mins walk to Leisure Centre (swimming pool, gym, spa, racket sports) 15 mins walk/5 mins drive to train station/central Bracknell

May 27 – Jun 3

G$16,258 GYD per night

Guest favorite

Guesthouse in Virginia Water

4.85 out of 5 average rating, 314 reviews

Cosy Cabin Virginia Water/Longcross

A separate, detached self contained cabin with private access, situated next to our home . Our cosy cabin has a cosy living area with sofa, a fully equipped kitchen area, separate bathroom with shower and a double bedroom with a 4ft double bed, wardrobe and drawers. Heating/air conditioning. Tea, coffee, sugar and milk provided. Driveway parking space available on request (driveway may not be suitable for large vehicles, however there is plenty of free on street parking)

Oct 27 – Nov 3

G$16,883 GYD per night

Guest favorite

Guesthouse in Eversley

4.97 out of 5 average rating, 316 reviews

Modern One Bedroom Private Ground Floor Annexe

Our modern Annexe is located next door to our main home. It has its own private access and parking to the front. Ideally located for easy access to the M3 & M4 motorway network and close to Rivervale Barn, Warbrook House & The Elvetham wedding venues. There are three very good Pubs within walking distance, all do superb food. All local amenities are close by. Wellington Country Park and California Country Park are also within close driving distance.

Feb 3 – 10

G$18,770 GYD per night

Guest favorite

Guesthouse in Buckinghamshire

4.98 out of 5 average rating, 220 reviews

The Barn at The Grove

The Barn is a self-contained recently converted space in the heart of the Chilterns. It is close to the riverside towns of Henley-on-Thames and Marlow and the surrounding Chiltern countryside. It is located on the edge of the village of Frieth with nearby farm shops and local gastro-pubs within a 5 min drive. The Barn is in a private and peaceful location with off-street parking. It is perfect for couples, solo travellers and small families.

Jul 21 – 28

G$25,437 GYD per night

Guest favorite

Guesthouse in Buckinghamshire

5.0 out of 5 average rating, 150 reviews

Red Kite Barn in a secluded valley close to Marlow

Red Kite Barn is situated in a lovely secluded valley (AONB), a 5 minute drive (25min walk) into Marlow, with its coffee shops, riverside walks and Michelin star dining. We are perfectly located for cycling or walking in the beautiful Chilterns and a short drive from Henley and Windsor. Heathrow is half an hour and fast trains go into London from Maidenhead. Red Kites, squirrels, foxes and deer are regular visitors to the garden.

Oct 20 – 27

G$30,123 GYD per night

Guest favorite

Guesthouse in Taplow

4.94 out of 5 average rating, 455 reviews

Luxury Rustic Log Cabin... secluded deck & garden

A luxury haven in lovely gardens adjacent to the main house. Secure private parking in large gravel drive. Ideal for Guests attending weddings/celebrations at Hedsor or Cliveden House Visiting The N.Trust Gardens, Tea or Spa Day at Cliveden as it’s on our doorstep! 8 miles to Windsor, visit the famous Castle. Beautiful walks by the River Thames, very pretty local villages with quaint country pubs Suitable for two guests

Oct 16 – 23

G$33,886 GYD per night

Guest favorite

Guesthouse in Abinger Hammer

4.97 out of 5 average rating, 243 reviews

The perfect hideaway, nestled in the Surrey Hills.

Nestled in the heart of The Surrey Hills (Area of Outstanding Natural Beauty), Abinger Hammer is a peaceful, historic village set on the banks of the Tillingbourne. It is the perfect country escape and an ideal destination for cyclists, hikers or for those just seeking a peaceful hideaway. Insta: @klb.surreyhills

Oct 10 – 17

G$21,017 GYD per night

Guest favorite

Guesthouse in Windsor and Maidenhead

4.96 out of 5 average rating, 142 reviews

1 Bedroom private property +free parking

A great self contained 1 bedroom property. A stone's throw away from Legoland Windsor Resort with a bus route right on your doorstep taking you to Windsor Castle, Slough and London. The property is within walking distance of the Queen's Royal Great Park. Perfect for a quiet weekend away!

Aug 14 – 21

G$24,703 GYD per night